Ten Style Hacks to Dress Like the Boss

Categories Fashion

The boss may have more money but observe some of his style cues and one day, you may be the man.

Keep fit

There’s a reason world leaders love being photographed completing triathlons and shooting hoops and wrestling sharks — it projects action, discipline, and vigour; all the qualities you want in a boss.



You don’t see many CEOs rocking the full-on Zach Galifianakis, who looks more like the bloke cleaning out the manager’s bin than the man occupying the seat itself.

Suit up

This is a no-brainer, but the style takes some work. Stick to serious, muted colours, perhaps in a pinstripe, but with no garish weave or pattern. Stick to muted, dark hues in general — lighter shades of blue and grey and brown are more casual, especially in a suit.


Tie your tie

A medium-width tie is where you can add a splash of colour to your workwear, so long as it’s in a fat double Windsor not, rather than the too-thin four-in-hand.

Stand up straight

Men with good posture carry more presence than Santa, filling the room, appearing taller and slimmer, and projecting power. Heard that advice about making yourself look as big as possible when you encounter a bear? Yeah, just like. Science.


From conservative options like Oxfords and Derbies to modern, on-trend brogues or monk straps, smart shoes complete the boss’ outfit. Oh, and shine them — or get someone to do it for you.



A small detail that wins over admirers — not too flashy, but provides great insight into the style and character of a man. Opt for a manly case diameter on the wide side — 41-46mm if you’ve got a wider wrist — rather than the more feminine 38mm that’s the current trend.



A flawless command of accessories communicates total control over your style, as if you’ve got the basics so down-pat you’ve got time to focus on the little things. We’re talking pocket squares, cufflinks, tie bars, and any jewellery restrained to a simple wedding band.

Man bag

Carrying a backpack with a suit is right up there with white socks and square-toed black shoes as the biggest fashion faux pas you can commit in the office. A leather satchel is the modern favourite while a vintage briefcase screams authority.

Master casual

Casual Fridays are a chance to display a little more personality to your colleagues, but not an invitation to wear jeans and joggers with your favourite footy jumper. Stick to a blazer with a T-shirt or button-down, for example, with chinos or dark denim and a suede desert boot or luxe sneaker.